4-Amino-1-(3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidin-2-one

ID: ALA1213618

Chembl Id: CHEMBL1213618

Cas Number: 78636-53-0

PubChem CID: 514806

Max Phase: Preclinical

Molecular Formula: C10H14FN3O4

Molecular Weight: 259.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2F)c(=O)nc1N

Standard InChI:  InChI=1S/C10H14FN3O4/c1-4-2-14(10(17)13-8(4)12)9-6(11)7(16)5(3-15)18-9/h2,5-7,9,15-16H,3H2,1H3,(H2,12,13,17)/t5-,6+,7-,9-/m1/s1

Standard InChI Key:  QZZJZXAWLQYJFK-JVZYCSMKSA-N

Alternative Forms

1. Parent:

   

   ALA1213618

   4-amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 259.24

Molecular Weight (Monoisotopic): 259.0968

AlogP: -1.28

#Rotatable Bonds: 2

Polar Surface Area: 110.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.72

CX Basic pKa: ┄

CX LogP: -1.51

CX LogD: -1.51

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.61

Np Likeness Score: 0.86

References

1. Watanabe KA, Su TL, Klein RS, Chu CK, Matsuda A, Chun MW, Lopez C, Fox JJ..  (1983)  Nucleosides. 123. Synthesis of antiviral nucleosides: 5-substituted 1-(2-deoxy-2-halogeno-beta-D-arabinofuranosyl)cytosines and -uracils. Some structure-activity relationships.,  26  (2): [PMID:6298422] [10.1021/jm00356a007]

2. Perlman ME, Watanabe KA, Schinazi RF, Fox JJ..  (1985)  Nucleosides. 133. Synthesis of 5-alkenyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosines and related pyrimidine nucleosides as potential antiviral agents.,  28  (6): [PMID:4009596] [10.1021/jm00383a009]

3. Krug PW, Schinazi RF, Hilliard JK..  (2010)  Inhibition of B virus (Macacine herpesvirus 1) by conventional and experimental antiviral compounds.,  54  (1): [PMID:19858259] [10.1128/aac.01435-08]

Source

Source(1):

• Scientific Literature